CN107108445B - 用于生产加香成分的中间体化合物 - Google Patents

用于生产加香成分的中间体化合物 Download PDF

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Publication number: CN107108445B
Authority: CN; China
Prior art keywords: methyl; inden; dihydro; nmr; dimethyl
Prior art date: 2015-01-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Active

Application number

CN201680005269.6A

Other languages

English (en)

Chinese (zh)

Other versions

CN107108445A (zh

Inventor

M·豪迪曼桑切斯

P·迪波

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Firmenich SA

Original Assignee

Firmenich SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2015-01-12

Filing date

2016-01-05

Publication date

2020-08-14

2016-01-05 Application filed by Firmenich SA filed Critical Firmenich SA

2017-08-29 Publication of CN107108445A publication Critical patent/CN107108445A/zh

2020-08-14 Application granted granted Critical

2020-08-14 Publication of CN107108445B publication Critical patent/CN107108445B/zh

Status Active legal-status Critical Current

2036-01-05 Anticipated expiration legal-status Critical

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238000004519 manufacturing process Methods 0.000 title claims abstract description 7
150000001875 compounds Chemical class 0.000 title claims description 39
239000004615 ingredient Substances 0.000 title abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 212
-1 Phenyl Chemical group 0.000 claims description 33
238000000034 method Methods 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
230000008569 process Effects 0.000 claims description 15
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 12
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
150000004702 methyl esters Chemical class 0.000 claims description 6
239000002243 precursor Substances 0.000 claims description 5
102000002322 Egg Proteins Human genes 0.000 claims description 4
108010000912 Egg Proteins Proteins 0.000 claims description 4
QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 4
210000003278 egg shell Anatomy 0.000 claims description 4
229940095102 methyl benzoate Drugs 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 3
238000009826 distribution Methods 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
230000009467 reduction Effects 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
QTGAIOGWZGBIRN-UHFFFAOYSA-N CC1=CC2=C(CC(C2=O)(C)CC(=O)O)C=C1 Chemical compound CC1=CC2=C(CC(C2=O)(C)CC(=O)O)C=C1 QTGAIOGWZGBIRN-UHFFFAOYSA-N 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 9
239000000126 substance Substances 0.000 abstract description 4
238000001311 chemical methods and process Methods 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 104
238000006243 chemical reaction Methods 0.000 description 40
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 39
238000005160 1H NMR spectroscopy Methods 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
150000002148 esters Chemical class 0.000 description 37
239000007788 liquid Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 19
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
150000002576 ketones Chemical class 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
UWSPWQQZFOSTHS-UHFFFAOYSA-N (2,5-dimethyl-1,3-dihydroinden-2-yl)methanol Chemical compound CC1=CC=C2CC(C)(CO)CC2=C1 UWSPWQQZFOSTHS-UHFFFAOYSA-N 0.000 description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
229910052739 hydrogen Inorganic materials 0.000 description 14
239000001257 hydrogen Substances 0.000 description 14
238000002360 preparation method Methods 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000004817 gas chromatography Methods 0.000 description 11
239000000047 product Substances 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 10
GWIILMGVMBOMGQ-UHFFFAOYSA-N 2-(hydroxymethyl)-2,5-dimethyl-3h-inden-1-one Chemical compound CC1=CC=C2C(=O)C(C)(CO)CC2=C1 GWIILMGVMBOMGQ-UHFFFAOYSA-N 0.000 description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
208000012839 conversion disease Diseases 0.000 description 7
238000004821 distillation Methods 0.000 description 7
230000007062 hydrolysis Effects 0.000 description 7
238000006460 hydrolysis reaction Methods 0.000 description 7
239000000243 solution Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
239000000758 substrate Substances 0.000 description 6
125000004665 trialkylsilyl group Chemical group 0.000 description 6
FFLDXLWVAGFFMF-UHFFFAOYSA-N 2,5-dimethyl-2,3-dihydroinden-1-one Chemical compound CC1=CC=C2C(=O)C(C)CC2=C1 FFLDXLWVAGFFMF-UHFFFAOYSA-N 0.000 description 5
239000005711 Benzoic acid Substances 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
239000002638 heterogeneous catalyst Substances 0.000 description 4
238000007327 hydrogenolysis reaction Methods 0.000 description 4
238000010926 purge Methods 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
BEKNOGMQVKBMQN-UHFFFAOYSA-N 2-methyl-2,3-dihydroinden-1-one Chemical class C1=CC=C2C(=O)C(C)CC2=C1 BEKNOGMQVKBMQN-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
238000010791 quenching Methods 0.000 description 3
239000007787 solid Substances 0.000 description 3
PMHDOAMHNLEBNG-UHFFFAOYSA-N (2-methyl-1,3-dihydroinden-2-yl)methanol Chemical class C1=CC=C2CC(C)(CO)CC2=C1 PMHDOAMHNLEBNG-UHFFFAOYSA-N 0.000 description 2
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
LVUAWUPZTUDEAW-UHFFFAOYSA-N 2,4,5-trimethyl-2,3-dihydroinden-1-one Chemical compound O=C1C(C)CC2=C1C=CC(C)=C2C LVUAWUPZTUDEAW-UHFFFAOYSA-N 0.000 description 2
ZDCQKZOFWPDZHL-UHFFFAOYSA-N 2,4-dimethyl-2,3-dihydroinden-1-one Chemical compound O=C1C(C)CC2=C1C=CC=C2C ZDCQKZOFWPDZHL-UHFFFAOYSA-N 0.000 description 2
BQJNORNRCBKRFK-UHFFFAOYSA-N 2,5,6-trimethyl-2,3-dihydroinden-1-one Chemical compound CC1=C(C)C=C2C(=O)C(C)CC2=C1 BQJNORNRCBKRFK-UHFFFAOYSA-N 0.000 description 2
MFCLOAFNUWAGGB-UHFFFAOYSA-N 2,6-dimethyl-2,3-dihydroinden-1-one Chemical compound C1=C(C)C=C2C(=O)C(C)CC2=C1 MFCLOAFNUWAGGB-UHFFFAOYSA-N 0.000 description 2
WGAIKEHHOKCOJR-UHFFFAOYSA-N 2-methyl-5-propan-2-yl-2,3-dihydroinden-1-one Chemical compound CC(C)C1=CC=C2C(=O)C(C)CC2=C1 WGAIKEHHOKCOJR-UHFFFAOYSA-N 0.000 description 2
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
YVPUMWPIDWKLKZ-UHFFFAOYSA-N C(C)(C)(C)[Si](C)(C)OCC1(CC2=CC=C(C=C2C1)C)C Chemical compound C(C)(C)(C)[Si](C)(C)OCC1(CC2=CC=C(C=C2C1)C)C YVPUMWPIDWKLKZ-UHFFFAOYSA-N 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000011068 loading method Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
XSZYQEYWYALJCG-UHFFFAOYSA-N (2,4,5-trimethyl-1,3-dihydroinden-2-yl)methanol Chemical compound CC1=CC=C2CC(C)(CO)CC2=C1C XSZYQEYWYALJCG-UHFFFAOYSA-N 0.000 description 1
HDMKKTOPNBPPJR-UHFFFAOYSA-N (2,4-dimethyl-1,3-dihydroinden-2-yl)methanol Chemical compound CC1=CC=CC2=C1CC(C)(CO)C2 HDMKKTOPNBPPJR-UHFFFAOYSA-N 0.000 description 1
YJPOCHHNTKJCQU-UHFFFAOYSA-N (2,5,6-trimethyl-1,3-dihydroinden-2-yl)methanol Chemical compound C1=C(C)C(C)=CC2=C1CC(C)(CO)C2 YJPOCHHNTKJCQU-UHFFFAOYSA-N 0.000 description 1
GGRYVDOLHBRDMQ-UHFFFAOYSA-N (2-methyl-5-propan-2-yl-1,3-dihydroinden-2-yl)methanol Chemical compound CC(C)C1=CC=C2CC(C)(CO)CC2=C1 GGRYVDOLHBRDMQ-UHFFFAOYSA-N 0.000 description 1
IQNHBUQSOSYAJU-UHFFFAOYSA-N 2,2,2-trifluoro-n-methylacetamide Chemical compound CNC(=O)C(F)(F)F IQNHBUQSOSYAJU-UHFFFAOYSA-N 0.000 description 1
QYVIDQDORQTCBS-UHFFFAOYSA-N 2-methylinden-1-one Chemical compound C1=CC=C2C(=O)C(C)=CC2=C1 QYVIDQDORQTCBS-UHFFFAOYSA-N 0.000 description 1
AFQLDWUNVQFNOC-UHFFFAOYSA-N CC1(C(C2=CC=C(C=C2C1)C)=O)CO[Si](C)(C)C(C)(C)C Chemical compound CC1(C(C2=CC=C(C=C2C1)C)=O)CO[Si](C)(C)C(C)(C)C AFQLDWUNVQFNOC-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
229910052772 Samarium Inorganic materials 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
238000005575 aldol reaction Methods 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229960004424 carbon dioxide Drugs 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000007429 general method Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004845 hydriding Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/34—Monohydroxylic alcohols containing six-membered aromatic rings and other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/04—Formic acid esters
- C07C69/06—Formic acid esters of monohydroxylic compounds
- C07C69/07—Formic acid esters of monohydroxylic compounds of unsaturated alcohols
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- C07C69/157—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/24—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with monohydroxylic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

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Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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IL253362B (en)	2018-03-29
IL253362A0 (en)	2017-08-31
US20180002260A1 (en)	2018-01-04
BR112017011285A2 (pt)	2018-12-11
US9981894B2 (en)	2018-05-29
JP2018505132A (ja)	2018-02-22
ES2735019T3 (es)	2019-12-13
WO2016113151A1 (fr)	2016-07-21
MX2017005988A (es)	2017-07-11
EP3245185B1 (fr)	2019-03-13
JP6698654B2 (ja)	2020-05-27
EP3245185A1 (fr)	2017-11-22
CN107108445A (zh)	2017-08-29

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